Dimethylcarbamoyl Chloride → HCID 54199536, compound

HRID 1995642Notes

Reaction equation

HRID 1995642 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:14])[S:8][C:7]2=[N:9][CH:10]=[CH:11][N:6]2[C:5]1=[N:12][OH:13].[CH3:15][N:16]([CH3:20])[C:17](Cl)=[O:18]>O1CCCC1>[CH3:3][C:4]1([CH3:14])[S:8][C:7]2=[N:9][CH:10]=[CH:11][N:6]2[C:5]1=[N:12][O:13][C:17](=[O:18])[N:16]([CH3:20])[CH3:15]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 71420982N-(2,2-Dimethylimidazo[2,1-b][1,3]thiazol-3(2H)-ylidene)hydroxylamine

Product 1

HCID 54199536HCID 54199536, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 330 mg (13.6 mmol) of sodium hydride in 150 ml of dry tetrahydrofuran was added 2.50 g (13.6 mmol) of 2,2-dimethyl-3-hydroxyimino-2,3-dihydroimidazo-[2,1-b]thiazole. The reaction mixture was stirred at 25° for 1 hour and cooled in an ice bath before 1.54 g (14.3 mmol) of dimethylcarbamoyl chloride was added. After stirring for 12 hours at 25°, the solvent was removed in vacuo and the residue washed with hexane, dissolved in methylene chloride. The methylene chloride solution was washed with water, dried (MgSO4), and concentrated in vacuo to give 2.94 g (85%) of desired product. m.p. 99°-102.5°.

Workup

  1. additionwas added
  2. stirringAfter stirring for 12 hours at 25°
  3. customthe solvent was removed in vacuo
  4. washthe residue washed with hexane
  5. dissolutiondissolved in methylene chloride
  6. washThe methylene chloride solution was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d05c476222749aba537a954b8fab002
Source dataset
uspto-grants-1983_09
Patent number
US04405632

Reaction notes

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